Dimethylaminopivalophenone

Dimethylaminopivalophenone

Identifiers
IUPAC name 3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one
CAS Number	15451-29-3
PubChem (CID)	84922
ChemSpider	76610
Chemical and physical data
Formula	C13H19NO
Molar mass	205.30 g·mol^−1
3D model (Jmol)	Interactive image
SMILES CN(CC(C(=O)C1=CC=CC=C1)(C)C)C
InChI InChI=1S/C13H19NO/c1-13(2,10-14(3)4)12(15)11-8-6-5-7-9-11/h5-9H,10H2,1-4H3 Key:WKJYCZMXCFRIEO-UHFFFAOYSA-N

Dimethylaminopivalophenone^[1][2] is an opioid analgesic.^[3] with a potency ½ that of morphine. It was initially discovered by Russian scientists in 1954 and subsequently rediscovered in the US in 1969.^[4] Its LD₅₀ in mice is 83 mg/kg.^[5] It has never been marketed commercially, likely due to its complicated synthesis, low potency, and lack of benefits compared to similarly potent opioid compounds.

See also

• Tapentadol
• List of opioids
• Opioid#Table of non-morphinan opioids
• Amylocaine, a topical anesthetic with a very similar SAR (the amine is a single methylene spacer unit more distant & oxygenated)

References

1. James H. Brewster; Ernest L. Eliel (2011). "Carbon-Carbon Alkylations with Amines and Ammonium Salts". Organic Reactions. 7 (3): 99–197. doi:10.1002/0471264180.or007.03.
2. Edward F. Kleinman (April 2011). "Dimethyl(methylene)ammonium Iodide". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd346.
3. Helmut Buschmann; Wolfgang Strassburger; Elmar Friderichs (24 January 2002). "Patent US 20020010178 - 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effect". Retrieved 2 October 2015.
4. Manmohan S. Atwal; Ludwig Bauer; S. N. Dixit; J. E. Gearien; M. Magahy; R. Morris; C. Pokorny (November 1969). "Analgetics. II. Relationship between structure and activity of some beta-amino ketones.". Journal of Medicinal Chemistry. 12 (6): 994–997. doi:10.1021/jm00306a006. PMID 5351480.
5. "2,2-dimethyl-3-(dimethylamino)-Propiophenone". ChemIDplus. Retrieved 2 October 2015.